Toluene → 3-acetyl-5-chloro-1-{1-[3-(3-acetyl-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one

HRID 2420355Notes

Reaction equation

HRID 2420355 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32].C[C:39]1[CH:44]=CC=CC=1.C(=O)([O-])[O-:46].[Na+].[Na+]>O>[C:31]([N:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:30]=[CH:29][C:5]=2[N:6]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([C:44](=[O:46])[CH3:39])[C:20]3=[O:28])[CH2:12][CH2:11]2)[C:7]1=[O:9])(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 1140TolueneHCID 3151DomperidoneHCID 7918Acetic AnhydrideHCID 10340Sodium Carbonate

Product 1

HCID 203856083-acetyl-5-chloro-1-{1-[3-(3-acetyl-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 parts of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one, 10 parts of acetic acid anhydride and 90 parts of methylbenzene is stirred and refluxed overnight. The reaction mixture is cooled, water is added and the whole is alkalized with a diluted sodium carbonate solution. The layers are separated and the organic phase is dried, filtered and evaporated. The residue is crystallized from methylbenzene. The product is filtered off and recrystallized from methylbenzene, yielding 4.5 parts of 3-acetyl-5-chloro-1-{1-[3-(3-acetyl-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one; mp. 185.3° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. customThe layers are separated
  4. customthe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from methylbenzene
  8. filtrationThe product is filtered off
  9. customrecrystallized from methylbenzene

Sources & evidence

ORD record
ord-14df77ae7f6e4fd4bf4bf36c7756aec5
Source dataset
uspto-grants-1978_08
Patent number
US04110333

Reaction notes

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